Herbicide

ABSTRACT

A herbicide containing as active constituent, in the presence of an inert carrier, an effective amount of one or several cumarilic acid amides of the general formula   WHEREIN R1 represents hydrogen, an alkyl radical with 1 - 3 carbon atoms or -OCH3; R2 hydrogen or an alkyl radical with 1 - 3 carbon atoms; R3 hydrogen or the methyl radical; R4, R5, R6 and R7 hydrogen, halogen, an alkyl radical with 1 - 3 carbon atoms, or -OCH3 and wherein of the radicals R4, R5, R6 and R7 at least three are hydrogen and only one is an other radical.

United States Patent [191 Briiunling et al.

[ Oct. 28, 1975 HERBICIDE [75] Inventors: Hermann Briiunling, Munich;Frank Miiller, Siegertsbrunn, Germany; Karl Milles, l-lolzkirchen, allof Germany [73] Assignee: Consortium fur Elektrochemische lndustrieGmbH, Munich, Germany [22] Filed: Nov. 12, 1973 [21] Appl. No.: 415,269

[30] Foreign Application Priority Data Nov. 21, 1972 Germany 2257034[52] US. Cl. 71/88 [51] Int. Cl? A01N 9/28 [58] Field of Search 71/88[56] References Cited UNITED STATES PATENTS 3,235,364 2/1966 Siegel71/88 3,689,507 9/1972 Gates et a]. 71/88 OTHER PUBLICATIONS McCabe etal., Chem. Abst., Vol. 49, 5383f. Rene et al., Chem. Abst. Vol. 76,(1972), 1129962.

Primary Examiner-Lewis Gotts Assistant Examiner-Catherine L. MillsAttorney, Agent, or Firm-Allis0n C. Collard [57] ABSTRACT A herbicidecontaining as active constituent, in the presence of an inert carrier,an effective amount of one or several cumarilic acid amides of thegeneral formula R R3 0 R c -N 6 \R2 9 Claims, No Drawings HERBICIDE Thepresent invention relates to a herbicide which contains as an activeingredient one or several cumab. Spraying powders contain in general;

30 80 percent by weight of active compound.

Some percent by weight of dispersing agents and, if

desired,

rilic acid amides of the formula 5 l 60 percent by weight of inertingredients such R R as kaolin, montmorillonite, china-clay, magnesium Lcarbonate, calcium carbonate, kieselgur, highly R 0 R dispersed silicicacid.

\ n l c. Dusting powders consist mostly of;

\ 1O 5 25 percent by weight of active ingredients, and

C N R6 0/ \R inert ingredients which may be the same as men- 2 tionedfor spraying powders.

R7 When the powders are made, the active ingredient is intimately mixedwith the other substances, then wherein ground to a grain size of mostlyless than p. on a R1 represents hydrogen, an alkyl radical with l 3sledge hammer mill or other suitable grinding device, carbon atoms ormixed once more, and finally passed through a sieve for R hydrogen or analkyl radical with l 3 carbon na lion 0 eac ive compoun saccor ing 0 eatoms, 20 ddt ht tll: t 'dbt tl:i

R3 hydrogen or the methyl radical invention, ot er nown active ingreients may e use belonging to the class of ureas, aryloxy fatty acids,tria- R R R and R hydrogen, halogen, an alkyl radical zines, carbamatesand thiolcarbamates, the dinitroalkyl with l 3 carbon atoms, or -OCH andwherein of anilines, acylanilides, and dinitrophenols for combined theradicals R R R and R at least three are hy- I effectiveness. By thesemeans, it is possible to increase drogen and only one 15 an otherradical.

, the activity or to improve the compatibility with the The preferredelements or radicals are the following: cultures i Hydrogen methyl OCH3or Ethyl In the following, the invention will be more fully de- R2hydrogen methyl or ethyl scribed in a number of examples, which aregiven by R3 hydrogen or methyl way of illustration but not oflimitation.

R R R R, hydrogen, chlorine, methyl or OCH EXAMPLE 1 (Preparation) Thecumarilic amides are known from the literature. T 1 d f h h b d However,it has now been discovered that a certain e ,genera 9 0 preparmg t e Cres according to the invention relates to the compounds group of thisclass of compounds has a herbicidal aclisted in the TABLE 1 hereinbelow.Where no refertion. More particularly, the compounds are effective in 3ence is made to the literature, the compounds have after-germination,where they have partly a selective been prepared here for the firsttime. action and are almost totally herbicidal. The preparation of thecumarilic acid amides is effected in a man- The cumanhc acid chloridecorrespondmg to the dek s b a t of th re tive hlo sired amide, isdissolved in ten times the amount of nown per 6 y re 0 e Spec c benzene.To the solution 2.1 mol ammonia is added rides with ammonia, or primaryor secondary amines, 40 per mol chloride used at a temperature of 0 0 ifnecessary with the addition of inert solvents immisciactually,appropriately Substituted amine or aque ble with water, such as benzene,diethyl ether, or chlo- Ous Solutions thereof may be added, in the caseof gflr tiv ingredems may be made into emulsion monia, methyl-anddimethylamine. After the addition 3 ac 6 1 is terminated, stirring iscontinued for another half concenffates, Powders for P Y or dustmgPowders hour at 30C. Subsequently the solution is shaken first accordingP known methods- I with 1/10 part by volume of water, calculated on theEmulslo" concentraies contfim volume of the benzene solution, then with2 N HCl, and

10 5O P Y 8 actlv? mgredlems twice with saturated sodium bicarbonatesolution.

25 80 Percent Y Welght organ? Solvents, -8- From the benzene solution,the cumarilic acid amide Zena, toluene, Xylene, cyclohexanone, isobtained after the solvent is dried over amhydrous propa butanol, g Yether, ethoxymethanol, sodium sulfate and evaporated in a water jetvacuum, butoxyethanol, and with a purity of 95 97% and a yield of 5 15Percfint y Weight dispersing agents, -g- When compounds are obtained asoily liquids, in-

m alkyl-b nz e sulfonate, Calcium Y 55 stead of the melting point we usefor characterization benzene sulfinate, alk l 01 1 col ether,condensathe osition of the roton resonance si nal of the h Y P Y8 Y P Pg Y tion products of alkylphenol and ethylene oxide, drogen atom inalpha position of the substituent of the and sodium alkylnaphthalenesulfonate. nitrogen atom. The 8-va lues for substance 2 (in the ta- Theyare made by intensive mixing of the ingredients ble) are at 2.92 ppm andfor substances 9 and 14 at in'a stirrer. 60 PP TABLE I Nr. R R R R, R RR, Fp. "C F Lit. "C

i CH, .CH;, H H H H H 34 36 34 36 2 CH; CH, CH: H H H H 01 k I59 61 3C,H C,H, CH, H H H H 61 63 64 4 CH3 CH3 CH3 H Cl H H 59 60 5 H H CH3 H HH H 142 44 145 6 H CH3 CH3 H H H H I23 25 124 25 7 C H C H H H Cl H H 5657 8 C:H: CZH: CH H Cl H H 56 53 TABLE I Cntinued Nr. R R, R R, R R6 RFp, c Fp. Lit. "c

9 C H C H,, CH; H CH; H H 01 10 H OCH CH H Cl H H 157 159 11 CH, 7 OCHCH H Cl H H 63 64 I2 ,.-C;,H ,,C H-, CH; H Cl H H 75 76 13 iC; H i-C H-,CH H C] H H 88 91 14 C,H C H CH H H CH H 52 54 EXAMPLE 2 TABLE 2 PlantsCom- Bar- Crab Mus- Corn Clea- Emu Co ate pound Corn ley Grass Oats tardBeets Flower vers Active lngredient 10 50% by weight 15 Cyclohexanone60% by weight 1 3 3 9 8 9 9 3 4 Xylene 5 20% by weight 2 3 2 9 l 3 l0 23 Emulsifier [HS 5 15% by weight 3 2 7 9 6 7 7 l 4 4 5 6 9 7 8 l0 2 4 5l 2 3 2 9 6 3 3 i 6 2 4 5 5 7 2 2 lHS 15 a mixture of sodium alkylbenzenesulfonate, al- 20 7 l0 7 7 8 8 8 7 9 kylpolyglycol ether andsolvent; "-15 is a commercial 2 :8 g 3 f, g 3 name of the ChemicalManufacturers l-liils (Germany). 12 6 l l l 1 l 0 1 l 3 8 2 2 1 3 4 O 0EXAMPLE 3 14 10 s 6 s 10 9 3 s Code:

Active ingredient Sodium sulfo succinic acid dioctyl ester Sodiumligninc-sulfonate Highly dispersed silicic acid Kaolin Spraying Powder3O 80% by weight 2 3% by weight 0 4% by weight 0 3% by weight 10 60% byweight EXAMPLE 4 Active ingredient Highly dispersed silicic acid Calciumcarbonate Dusting Powder 5 25% by weight 00 1% by weight 70 95% byweight EXAMPLE 5 Testing for herbicidal properties;

The following plants were set out in dishes in a glass (green) house:

(Corn) Zea-Mays (Oats) Arena Fama (Cleavers) Gallium Aparine (Barley)Hordeum (Mustard) Sinapis (Sugar Beets) Beta (Crab Grass) Digilaria(Corn Flower) Cenlaurea emulsion concentrate in the following manner:

Active ingredient Cyclohexanone Xylene Emulsifier lHS (as aboveexplained ing. Table 2 shows the results.

20% by weight 50% by weight 20% by weight 10% by weight Evaluationoccurred the last time 28 daysafter sprayno action l0= plants completelydestroyed As table 2 shows, compounds 1 and 3 attack weeds in corn to alarge extent without damaging the culture plants. On the other hand,preparations 9 and 14 are herbicides which may be used with ornamentalplants belonging to the genus of centaurea (corn flower).

While the product of the present invention has been described mainly inrespect to only a few specific examples for purposes ofa complete anddetailed disclosure, it will be readily apparent to those skilled in theart that many other embodiments and modifications are within the purviewof this invention. Accordingly, the instance invention should not beconstrued as limited in any particulars except as recited in theappended claims or required by the prior art.

What is claimed is:

l. A method of destroying undesirable vegetation which comprisesapplying to said vegetation a herbicidally effective amount of aherbicide containing as active ingredient, in an inert carrier, at leastone cumarilic acid amide of the formula wherein R is selected from thegroup consisting of hydrogen, alkyl having 1 to 3 carbon atoms, andOCl-l R is selected from the group consisting of hydrogen and alkylhaving 1 to 3 carbon atoms; R is selected from the group consisting ofhydrogen and methyl;

R R R and R are selected from the group consisting of hydrogen, halogen,alkyl having 1 to 3 carbon atoms, and OCH and wherein of the radicals RR R and R at least three are hydrogen and only one is another radical.

2. The method of claim 1 wherein R is selected from the group consistingof hydrogen, methyl, ethyl and OCl-l 3. The method of claim 1 in which Ris selected from the group consisting of hydrogen, methyl and ethyl.

4. The method of claim 1 in which R is selected from the groupconsisting of hydrogen and methyl.

5. The method of claim 1 in which of the substituents R R R and R-,, atleast three are hydrogen and the fourth is selected from the groupconsisting of hydrogen, chlorine, methyl, and OCH 6. The method of claim1 in which said herbicide is applied as an emulsion concentrate havingthe following composition:

weight of active ingredient and 10 60% by weight of inert ingredients 9.The method of claim 1 in which said herbicide has a grain size of lessthan 20 [.L.

1. A METHOD OF DESTROYING UNDESIRABLE VEGETATION WHICH COMPRISESAPPLYING TO SAID VEGETATION A HERBICIDALLY EFFECTIVE AMOUNT OF AHERBICIDE CONTAINING AS ACTIVE INGREDIENT, IN AN INERT CARRIER, AT LEASTONE EUMARILIC ACID AMIDE OF THE FORMULA
 2. The method of claim 1 whereinR1 is selected from the group consisting of hydrogen, methyl, ethyl and-OCH3.
 3. The method of claim 1 in which R2 is selected from the groupconsisting of hydrogen, methyl and ethyl.
 4. The method of claim 1 inwhich R3 is selected from the group consisting of hydrogen and methyl.5. The method of claim 1 in which of the substituents R4, R5, R6 and R7,at least three are hydrogen and the fourth is selected from the groupconsisting of hydrogen, chlorine, methyl, and -OCH3.
 6. The method ofclaim 1 in which said herbicide is applied as an emulsion concentratehaving the following composition: 10 - 50% by weight of activeingredient 20 - 80% by weight of organic solvent, and 5 - 15% by weightof a dispersing agent.
 7. The method of claim 1 in which said herbicideis applied as a spraying powder having the following composition: 30 -80% by weight of active ingredient 10 - 60% by weight of inertingredients, and small percentage of a dispersing agent.
 8. The methodof claim 1 in which said herbicide is applied as a dusting powdercontaining 5 to 25% by weight of active ingredient and 10 - 60% byweight of inert ingredients.
 9. The method of claim 1 in which saidherbicide has a grain size of less than 20 Mu .